2-ethoxy-6-methyl-4-morpholino-5-nitropyrimidine | 186047-42-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-ethoxy-6-methyl-4-morpholino-5-nitropyrimidine
• 英文别名: 4-(2-Ethoxy-6-methyl-5-nitropyrimidin-4-yl)morpholine
• CAS: 186047-42-7
• 化学式: C₁₁H₁₆N₄O₄
• 分子量: 268.272
• InChiKey: VAXRZBQZQAFBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-ethoxy-6-methyl-4-morpholino-5-nitropyrimidine 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以23%的产率得到4-[6-(Dibromomethyl)-2-ethoxy-5-nitropyrimidin-4-yl]morpholine
  参考文献：
  名称：

  Synthesis and Evaluation of 6-(Dibromomethyl)-5-nitropyrimidines as Potential Antitumor Agents

  摘要：

  A series of 2,4,6-trisubstituted-5-nitropyrimidines have been prepared and evaluated for inhibition of proliferation of L1210 and H.Ep.2 cells in vitro. The most potent compound was 6-(dibromomethyl)-2-methoxy-4-morpholino-5-nitropyrimidine (11) (L1210, IC50 0.32 mu M; H.Ep.2, IC50 = 1.6 mu M). Of the 6-substituents incorporated, only CHBr2, CH2Br, and CHO were compatible with antiproliferative activity, while a wider variety of 4-substituents were tolerated. At concentrations near the IC50 for antiproliferative activity, a delayed resumption of cell proliferation in L1210 cultures indicated that the activity of the compounds was short-lived and suggested they might act by an alkylation mechanism.

  DOI：

  10.1021/jm9605546
• 作为产物：
  描述：

  2,4-二氯-5-硝基-6-甲基嘧啶 以 乙醚 、 乙醇 为溶剂， 反应 3.0h， 生成 2-ethoxy-6-methyl-4-morpholino-5-nitropyrimidine
  参考文献：
  名称：

  Synthesis and Evaluation of 6-(Dibromomethyl)-5-nitropyrimidines as Potential Antitumor Agents

  摘要：

  A series of 2,4,6-trisubstituted-5-nitropyrimidines have been prepared and evaluated for inhibition of proliferation of L1210 and H.Ep.2 cells in vitro. The most potent compound was 6-(dibromomethyl)-2-methoxy-4-morpholino-5-nitropyrimidine (11) (L1210, IC50 0.32 mu M; H.Ep.2, IC50 = 1.6 mu M). Of the 6-substituents incorporated, only CHBr2, CH2Br, and CHO were compatible with antiproliferative activity, while a wider variety of 4-substituents were tolerated. At concentrations near the IC50 for antiproliferative activity, a delayed resumption of cell proliferation in L1210 cultures indicated that the activity of the compounds was short-lived and suggested they might act by an alkylation mechanism.

  DOI：

  10.1021/jm9605546